As a young punk, I used to wear pyjamas ironically. Now, I just wear them. They are my uniform. I don’t get out of the house to perform much any more, but when I was asked recently to host Pajama-Rama – “a fundraiser with an emphasis on fun” – at my daughter’s elementary school, how could I say no? I was already dressed for it.

I had to open the show, move things along between nervous children reading books. I did okay. Some of my stuff was “out there.” I tried a piece, couldn’t help myself, where I asked the principal to come up so she and I could act out the Hot For Teacher video. It sort of fell apart. My daughter stared up at her dad, a middle-aged man in his flop-sweat-stained tartan pyjamas. After the show, a couple of people said, “Wow, you’re hosting this? That’s cool.” Cool? It was probably anything but.

I feel like I was once young and cool and then I woke up in the middle of my life emptying the dishwasher. I’m getting older. I suddenly understand the appeal of golf. It’s the only sport where the pros look like the fans. I remember a time when doctors smoked in the hallways of hospitals. A time when you could talk your way out of a DUI. When a DJ was just some jerk playing records at a party – me, I suppose.

Nowadays I’m no DJ. And I’ve been ruminating on the notion of cool. Which means, by definition, I’m not.

Last week, I was asked to do a guest spot on Workaholics, a “hot” sitcom on Comedy Central. The Black Keys were also in the show. I’d like to say that they didn’t know who I was, but they did. They looked at me across the set, time-adjusted my face and remembered they were fans of the Kids in the Hall. They asked if I was performing anywhere. I told them about Pajama-Rama. I hated myself, but I was going to have to ask for a photo. It used to be the other way around.

I know I am not part of the self-portrait generation, happily taking pictures holding drinks in bars and uploading them to Flickr. So how then did I recently find myself trying to get an iPhone pic with the Black Keys? I don’t Facebook or Twitter. What use would I possibly have for such a photo? Would I send it to myself to prove I hadn’t lost my cool?

That got me thinking about Mötley Crüe. They just held an Internet press conference to announce they were going on tour and remind us that they “still really rock.” And are “totally relevant.” They are old. They could actually take their withered arms and fold them like the back of a Mad magazine cover and their Mötley Crüe tattoos would become what? Moby? Muse? Miley Cyrus? Mötley Crüe are uncool because they always have been. Age has nothing to do with it.

As we get older, how can one tell “what’s in, what’s out?” Presumably by turning to a What’s Hot, What’s Not list. I was reading one such list recently. Do you know who’s not hot? Betty White. Are you kidding me? She’s 90. She was already a baffled senior when the Beatles broke. For heaven’s sake, leave the poor woman alone. What’s hot – orange. What’s not – blue. Oh dear, who’s gonna break it to the rainbow? By the way, What’s Hot lists have been replaced with the term “trending.” We now live in a world where a What’s Hot list is not. Cool has become a snake that eats its own tail, a circle with forward momentum.

Last week, when Beastie Boy Adam Yauch died, I thought, “Wow, that guy was cool.” The Beastie Boys’ music was important to the Kids In The Hall. I’d like to count them as peers, but they played arenas and we played theatres. And, truth be told, sometimes casinos. But Adam remained cool, not because he was huge but because he evolved. He moved past the world view that his youthful anger created for him.

In your 20s, you think about what the world can give you. In your 30s, what the world thinks of you. In your 40s and beyond, what you think of the world. Today, I think the world is a place savage as it is beautiful, a place happy as it is sad. As we get older, competition leaves us, and anger morphs into something more. What replaces it, hopefully, is humanity.

The dark comedian in me wonders if Adam’s last words were, “I won the fight for your right to party, but sadly I’ve lost the fight with cancer.” The humanist in me knows his last words were probably about mindfulness, peace and the people who loved him.

Bruce McCulloch is currently in development on a series for CTV and another series for CBS.